Hall of Famer Curlin, the 2007 Preakness (G1) winner, has a total of four grandsons – half the field – in Saturday’s 148th running at Pimlico. Curlin’s champion son Good Magic is single-handedly responsible for three of them, led by Kentucky Derby (G1) hero Mage.

Mage can boast that both of his grandsires captured the Preakness. His dam, Puca, is by Big Brown, who romped in the middle jewel after a similarly dominant display in the 2008 Kentucky Derby. Mage emulated Big Brown by winning the Derby in only his fourth career start, and now he’ll try to follow in his hoofsteps again by adding the Preakness trophy.
Mage’s Preakness connections extend further in his dam’s (mother’s) side. His great-granddam is a daughter of 1990 Preakness star Summer Squall, who turned the tables on Derby winner Unbridled at Pimlico. Mage’s female line traces to the same ancestress as champion Afleet Alex, who scored in a particularly memorable Preakness in 2005. Afleet Alex clipped heels when a rival veered turning into the stretch, but miraculously stayed on his feet and recovered to win well. He went on to rout the Belmont (G1) and join the “two-thirds club,” as the winner of two jewels of the Triple Crown.
Good Magic, runner-up to Triple Crown winner Justify in the 2018 Kentucky Derby, battled him early in the Preakness before succumbing in a close fourth. Now that he’s sired a Derby winner in Mage, Good Magic hopes to collect another classic victory from his bumper first crop. Blazing Sevens and Perform will give him two more solid chances in the middle jewel.
Perform’s dam is by Tale of Ekati, the 2008 Wood Memorial (G1) winner and fourth in Big Brown’s Derby. Tale of Ekati sired Tale of Verve, whose career highlight was finishing second to American Pharoah in the 2015 Preakness. 
Perform descends from Broodmare of the Year Leslie’s Lady, dam of leading sire Into Mischief, promising young stallion Mendelssohn, and Hall of Famer Beholder. From the family of 2012 Derby and Preakness hero I’ll Have Another, Perform shares the same remote ancestress as 1978 Triple Crown sweeper Affirmed, and even further back, 1958 Derby and Preakness scorer Tim Tam.
Curlin’s fourth grandson in the line-up is Coffeewithchris, by 2014 Preakness runner-up Ride on Curlin. He was just the first of Curlin’s progeny to run well in the middle jewel. In 2016, Curlin’s son Exaggerator won, putting Curlin in exalted company as a Preakness winner to sire a Preakness winner. Another son, Tenfold, placed third in 2018 by edging Good Magic.
The success of Good Magic at stud has revived memories, not only of the 2018 classics, but the 2007 Triple Crown trail as well. Good Magic is out of a mare by one of Curlin’s main opponents that season, Hard Spun.
So it’s apropos that another leading actor from 2007, Kentucky Derby champion Street Sense, renews their rivalry with a son of his own here – First Mission. Street Sense prevailed at Churchill Downs, but not at Pimlico, where Curlin outdueled him. Now First Mission aims to land a blow for Street Sense against the Curlin posse.
First Mission has maternal ties to Rachel Alexandra, the Hall of Famer who beat males in the 2009 Preakness, Haskell (G1), and Woodward (G1). First Mission’s dam is bred along the same lines as Rachel Alexandra, both being daughters of Medaglia d’Oro and out of mares by Forty Niner’s son Roar. Moreover, First Mission and Rachel Alexandra trace to the same early 19th-century ancestress, Wire, the third-placer in the 1814 Oaks at Epsom. 
Medaglia d’Oro, a $5.7 million-earner in his career, competed in all three jewels of the 2002 Triple Crown. Just a half-length shy when second in the Belmont, he was a decent fourth in the Derby, but threw in the worst race of his life when eighth in the Preakness. 
Like Curlin, Medaglia d’Oro has four descendants in Preakness 148. One hails from his sire line, Chase the Chaos, by Medaglia d’Oro’s Australian Group 1-winning son Astern. Chase the Chaos comes from the extended family of 2013 Preakness hero Oxbow.
The other three count “Medaglia” as an ancestor on their dam’s side. Aside from the aforementioned First Mission, Blazing Sevens is out of a mare by Medaglia’s son Warrior’s Reward, while National Treasure’s dam is by Medaglia himself.
National Treasure’s sire, multiple Grade 1 star Quality Road, missed the 2009 classics due to foot problems. But National Treasure’s female line includes full sisters to winners of five jewels between them. He descends from Sin Igual, whose brother Assault swept the 1946 Triple Crown; and she in turn traces to Masda, sister to the immortal Man o’ War. Skipping the 1920 Derby by the fixed determination of owner Sam Riddle, Man o’ War crushed the Preakness and Belmont. 
If Red Route One can pull an upset, sire Gun Runner would achieve the rare feat of getting back-to-back Preakness winners, after Early Voting (2022) put him on the scoreboard. And he’d be the only one to do so in his first two crops. 
Calumet patriarch Bull Lea was responsible for Faultless (1947) and Citation (1948), and the legendary Lexington sired the trio of Tom Ochiltree (1875), Shirley (1876), and Duke of Magenta (1878). Early 20th-century sire Broomstick had three winners, but none in consecutive years – Holiday (1914), Broomspun (1921), and Bostonian (1927).
Other sires with two Preakness winners are *Leamington (Harold in 1879 and Saunterer in 1881), *Watercress (Watervale in 1911 and Rhine Maiden in 1915), Fair Play (Man o’ War in 1920 and Display in 1926), *Sir Gallahad III (1930 Triple Crown star Gallant Fox and High Quest in 1934), *Nasrullah (Nashua in 1955 and Bold Ruler in 1957), Sovereign Dancer (Gate Dancer in 1984 and Louis Quatorze in 1996), Woodman (Hansel in 1991 and Timber Country in 1995), and Smart Strike (Curlin in 2007 and Lookin at Lucky in 2010).
Gun Runner’s sire, Candy Ride, would celebrate a hat trick as a paternal grandsire. The 2021 Preakness winner, Rombauer, is by another son of Candy Ride, Twirling Candy. Last year, Candy Ride had an exacta of grandchildren, as Early Voting beat Epicenter, who is out of a Candy Ride mare. 
Red Route One has plenty of pedigree power on his dam’s side as well. He is out of the Tapit mare Red House, an unraced full sister to champion filly Untapable. They are also half-sisters to Grade 1-winning millionaire Paddy O’Prado. Although his wins came on turf, Paddy O’Prado was third in the 2010 Kentucky Derby before regressing to sixth in the Preakness.
Following the matrilineal thread much further back, Red Route One has a common ancestress with 1957 Preakness star Bold Ruler, a Hall of Famer and leading sire who bequeathed us Secretariat. 
Turning to the sire lines, seven of the eight entrants represent the male line of Hall of Famer Native Dancer, who rebounded from his lone career loss in the 1953 Kentucky Derby to win both the Preakness and Belmont. The septet traces from various branches of his grandson Mr. Prospector – Smart Strike (the Curlin clan), Machiavellian/Street Cry (First Mission), Gone West (National Treasure), and Fappiano (Red Route One).
Chase the Chaos descends from the sire line of Northern Dancer, the 1964 Derby and Preakness champion. But the supersire factors elsewhere in the pedigrees of every other Preakness contender.
All-time great Secretariat, who made a spectacular leap into contention in his Preakness victory, likewise counts as an ancestor of all the runners here. The 1973 Triple Crown legend has become essential in modern bloodlines, having sired the dams of Storm Cat, Gone West, and A.P. Indy.